CA1225794A - Crosslinked hydrophilic copolymers, their preparation and their use - Google Patents

Crosslinked hydrophilic copolymers, their preparation and their use

Info

Publication number: CA1225794A
Authority: CA; Canada
Prior art keywords: formula; carbon atoms; alkyl; group; weight
Prior art date: 1983-04-22
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA000452440A

Other languages

English (en)

French (fr)

Inventor

Friedrich Engelhardt

Klaus Kuhlein

Juliane Balzer

Walter Dursch

Hans-Jerg Kleiner

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Sanofi Aventis Deutschland GmbH

Original Assignee

Cassella AG

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1983-04-22

Filing date

1984-04-19

Publication date

1987-08-18

1984-04-19 Application filed by Cassella AG filed Critical Cassella AG

1987-08-18 Application granted granted Critical

1987-08-18 Publication of CA1225794A publication Critical patent/CA1225794A/en

Status Expired legal-status Critical Current

Links

238000002360 preparation method Methods 0.000 title claims abstract description 15
229920001480 hydrophilic copolymer Polymers 0.000 title description 3
229920001577 copolymer Polymers 0.000 claims abstract description 60
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 49
125000000217 alkyl group Chemical group 0.000 claims abstract description 29
239000000178 monomer Substances 0.000 claims abstract description 26
239000001257 hydrogen Substances 0.000 claims abstract description 16
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
238000004132 cross linking Methods 0.000 claims abstract description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
150000002148 esters Chemical class 0.000 claims abstract description 6
239000003795 chemical substances by application Substances 0.000 claims abstract 2
-1 methylol group Chemical group 0.000 claims description 26
238000000034 method Methods 0.000 claims description 15
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 13
239000003431 cross linking reagent Substances 0.000 claims description 13
150000001768 cations Chemical class 0.000 claims description 11
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 8
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 7
238000009826 distribution Methods 0.000 claims description 6
125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 6
125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 6
229910052783 alkali metal Inorganic materials 0.000 claims description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
239000003054 catalyst Substances 0.000 claims description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
150000002431 hydrogen Chemical group 0.000 claims description 5
125000001918 phosphonic acid ester group Chemical group 0.000 claims description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 4
230000002378 acidificating effect Effects 0.000 claims description 4
150000001340 alkali metals Chemical class 0.000 claims description 4
125000005392 carboxamide group Chemical group NC(=O)* 0.000 claims description 4
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
150000003863 ammonium salts Chemical class 0.000 claims description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims description 3
238000010438 heat treatment Methods 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
125000005236 alkanoylamino group Chemical group 0.000 claims description 2
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 2
229940050176 methyl chloride Drugs 0.000 claims description 2
MNQOPPDTVHYCEZ-UHFFFAOYSA-N n-(hydroxymethyl)formamide Chemical compound OCNC=O MNQOPPDTVHYCEZ-UHFFFAOYSA-N 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
230000000875 corresponding effect Effects 0.000 claims 3
239000007795 chemical reaction product Substances 0.000 claims 2
125000004093 cyano group Chemical group *C#N 0.000 claims 1
239000004568 cement Substances 0.000 abstract description 10
ZTWTYVWXUKTLCP-UHFFFAOYSA-N vinylphosphonic acid Chemical compound OP(O)(=O)C=C ZTWTYVWXUKTLCP-UHFFFAOYSA-N 0.000 abstract description 7
238000004043 dyeing Methods 0.000 abstract description 4
239000007788 liquid Substances 0.000 abstract description 4
238000000576 coating method Methods 0.000 abstract description 3
239000000463 material Substances 0.000 abstract description 3
238000005538 encapsulation Methods 0.000 abstract description 2
238000010521 absorption reaction Methods 0.000 abstract 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
229920000642 polymer Polymers 0.000 description 25
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
239000000203 mixture Substances 0.000 description 18
239000002253 acid Substances 0.000 description 17
239000000243 solution Substances 0.000 description 15
239000000499 gel Substances 0.000 description 14
150000003254 radicals Chemical class 0.000 description 14
150000001875 compounds Chemical class 0.000 description 11
239000000047 product Substances 0.000 description 11
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
239000002904 solvent Substances 0.000 description 10
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
229910052757 nitrogen Inorganic materials 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000007864 aqueous solution Substances 0.000 description 6
238000001914 filtration Methods 0.000 description 6
239000000126 substance Substances 0.000 description 6
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 5
LXEKPEMOWBOYRF-UHFFFAOYSA-N [2-[(1-azaniumyl-1-imino-2-methylpropan-2-yl)diazenyl]-2-methylpropanimidoyl]azanium;dichloride Chemical compound Cl.Cl.NC(=N)C(C)(C)N=NC(C)(C)C(N)=N LXEKPEMOWBOYRF-UHFFFAOYSA-N 0.000 description 5
239000002585 base Substances 0.000 description 5
239000007789 gas Substances 0.000 description 5
229930195733 hydrocarbon Natural products 0.000 description 5
239000002002 slurry Substances 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical group CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
229910021529 ammonia Inorganic materials 0.000 description 4
239000012043 crude product Substances 0.000 description 4
JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 4
238000001035 drying Methods 0.000 description 4
239000000839 emulsion Substances 0.000 description 4
239000004744 fabric Substances 0.000 description 4
150000002430 hydrocarbons Chemical class 0.000 description 4
229920002521 macromolecule Polymers 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
239000004160 Ammonium persulphate Substances 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 3
235000019395 ammonium persulphate Nutrition 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 3
239000003995 emulsifying agent Substances 0.000 description 3
239000005337 ground glass Substances 0.000 description 3
230000006698 induction Effects 0.000 description 3
239000003999 initiator Substances 0.000 description 3
210000000056 organ Anatomy 0.000 description 3
238000001556 precipitation Methods 0.000 description 3
238000010992 reflux Methods 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
230000008961 swelling Effects 0.000 description 3
238000012360 testing method Methods 0.000 description 3
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 3
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
229920000742 Cotton Polymers 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
HFCYZXMHUIHAQI-UHFFFAOYSA-N Thidiazuron Chemical compound C=1C=CC=CC=1NC(=O)NC1=CN=NS1 HFCYZXMHUIHAQI-UHFFFAOYSA-N 0.000 description 2
150000008065 acid anhydrides Chemical class 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
JEHKKBHWRAXMCH-UHFFFAOYSA-N benzenesulfinic acid Chemical compound O[S@@](=O)C1=CC=CC=C1 JEHKKBHWRAXMCH-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
XHDNNRGTROLZCF-UHFFFAOYSA-N ethenyl(methoxy)phosphinic acid Chemical compound COP(O)(=O)C=C XHDNNRGTROLZCF-UHFFFAOYSA-N 0.000 description 2
238000005755 formation reaction Methods 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
125000005395 methacrylic acid group Chemical group 0.000 description 2
238000002156 mixing Methods 0.000 description 2
ODYNBECIRXXOGG-UHFFFAOYSA-N n-butylbutan-1-amine;hydron;chloride Chemical compound [Cl-].CCCC[NH2+]CCCC ODYNBECIRXXOGG-UHFFFAOYSA-N 0.000 description 2
239000012875 nonionic emulsifier Substances 0.000 description 2
239000012188 paraffin wax Substances 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
239000011435 rock Substances 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000007787 solid Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
230000009974 thixotropic effect Effects 0.000 description 2
229920002554 vinyl polymer Polymers 0.000 description 2
239000008096 xylene Substances 0.000 description 2
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
YROIHKKJDMNYRB-UHFFFAOYSA-N 2-acetyloxyethylphosphonic acid Chemical compound CC(=O)OCCP(O)(O)=O YROIHKKJDMNYRB-UHFFFAOYSA-N 0.000 description 1
MUZDXNQOSGWMJJ-UHFFFAOYSA-N 2-methylprop-2-enoic acid;prop-2-enoic acid Chemical compound OC(=O)C=C.CC(=C)C(O)=O MUZDXNQOSGWMJJ-UHFFFAOYSA-N 0.000 description 1
AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
IUNVCWLKOOCPIT-UHFFFAOYSA-N 6-methylheptylsulfanyl 2-hydroxyacetate Chemical compound CC(C)CCCCCSOC(=O)CO IUNVCWLKOOCPIT-UHFFFAOYSA-N 0.000 description 1
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
239000004342 Benzoyl peroxide Substances 0.000 description 1
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 1
102100024133 Coiled-coil domain-containing protein 50 Human genes 0.000 description 1
229920008712 Copo Polymers 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
101000910772 Homo sapiens Coiled-coil domain-containing protein 50 Proteins 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
RSPISYXLHRIGJD-UHFFFAOYSA-N OOOO Chemical compound OOOO RSPISYXLHRIGJD-UHFFFAOYSA-N 0.000 description 1
JLNTWVDSQRNWFU-UHFFFAOYSA-N OOOOOOO Chemical compound OOOOOOO JLNTWVDSQRNWFU-UHFFFAOYSA-N 0.000 description 1
MOMWFXLCFJOAFX-UHFFFAOYSA-N OOOOOOOO Chemical compound OOOOOOOO MOMWFXLCFJOAFX-UHFFFAOYSA-N 0.000 description 1
CQGRLHBOVUGVEA-UHFFFAOYSA-N OOOOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOOOO CQGRLHBOVUGVEA-UHFFFAOYSA-N 0.000 description 1
NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 1
208000036366 Sensation of pressure Diseases 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
239000003463 adsorbent Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
229910001870 ammonium persulfate Inorganic materials 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
235000019400 benzoyl peroxide Nutrition 0.000 description 1
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
150000003857 carboxamides Chemical class 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
238000007596 consolidation process Methods 0.000 description 1
238000007334 copolymerization reaction Methods 0.000 description 1
239000002537 cosmetic Substances 0.000 description 1
150000001923 cyclic compounds Chemical class 0.000 description 1
229960002887 deanol Drugs 0.000 description 1
230000007423 decrease Effects 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
238000010586 diagram Methods 0.000 description 1
125000005265 dialkylamine group Chemical group 0.000 description 1
WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 1
238000005553 drilling Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003792 electrolyte Substances 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical class NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
239000007863 gel particle Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
238000000227 grinding Methods 0.000 description 1
150000002366 halogen compounds Chemical class 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
229920001477 hydrophilic polymer Polymers 0.000 description 1
230000002209 hydrophobic effect Effects 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
235000013847 iso-butane Nutrition 0.000 description 1
238000009533 lab test Methods 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
PNLUGRYDUHRLOF-UHFFFAOYSA-N n-ethenyl-n-methylacetamide Chemical compound C=CN(C)C(C)=O PNLUGRYDUHRLOF-UHFFFAOYSA-N 0.000 description 1
ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229910000069 nitrogen hydride Inorganic materials 0.000 description 1
229920000847 nonoxynol Polymers 0.000 description 1
235000014571 nuts Nutrition 0.000 description 1
150000001451 organic peroxides Chemical class 0.000 description 1
238000009980 pad dyeing Methods 0.000 description 1
239000002245 particle Substances 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
239000000985 reactive dye Substances 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000011084 recovery Methods 0.000 description 1
230000000979 retarding effect Effects 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
239000004289 sodium hydrogen sulphite Substances 0.000 description 1
BWYYYTVSBPRQCN-UHFFFAOYSA-M sodium;ethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=C BWYYYTVSBPRQCN-UHFFFAOYSA-M 0.000 description 1
239000002689 soil Substances 0.000 description 1
125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000004753 textile Substances 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
239000007762 w/o emulsion Substances 0.000 description 1
238000010792 warming Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/52—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing synthetic macromolecular substances
- D06P1/5207—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/42—Use of materials characterised by their function or physical properties
- A61L15/60—Liquid-swellable gel-forming materials, e.g. super-absorbents
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B24/00—Use of organic materials as active ingredients for mortars, concrete or artificial stone, e.g. plasticisers
- C04B24/003—Phosphorus-containing compounds
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B24/00—Use of organic materials as active ingredients for mortars, concrete or artificial stone, e.g. plasticisers
- C04B24/24—Macromolecular compounds
- C04B24/28—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F230/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing phosphorus
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F246/00—Copolymers in which the nature of only the monomers in minority is defined

Landscapes

Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Chemistry (AREA)
Ceramic Engineering (AREA)
Materials Engineering (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Structural Engineering (AREA)
Hematology (AREA)
Public Health (AREA)
Textile Engineering (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Dispersion Chemistry (AREA)
Veterinary Medicine (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Steroid Compounds (AREA)
Paints Or Removers (AREA)
Saccharide Compounds (AREA)
Medicinal Preparation (AREA)
Coloring (AREA)
Compositions Of Macromolecular Compounds (AREA)

CA000452440A 1983-04-22 1984-04-19 Crosslinked hydrophilic copolymers, their preparation and their use Expired CA1225794A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19833314569 DE3314569A1 (de)	1983-04-22	1983-04-22	Vernetzte hydrophile copolymerisate, ihre herstellung und verwendung
DEP3314569.5		1983-04-22

Publications (1)

Publication Number	Publication Date
CA1225794A true CA1225794A (en)	1987-08-18

Family

ID=6197044

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000452440A Expired CA1225794A (en)	1983-04-22	1984-04-19	Crosslinked hydrophilic copolymers, their preparation and their use

Country Status (8)

Country	Link
US (1)	US4585845A (de)
EP (1)	EP0123297B1 (de)
JP (1)	JPS6042403A (de)
AT (1)	ATE36168T1 (de)
BR (1)	BR8401839A (de)
CA (1)	CA1225794A (de)
DE (2)	DE3314569A1 (de)
NO (1)	NO841405L (de)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
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GB8526367D0 (en) *	1985-10-25	1985-11-27	Wilson A D	Cement-forming compositions
EP0473881B1 (de) *	1990-09-03	2001-11-07	Showa Denko Kabushiki Kaisha	Flüssigkeitsabsorbierendes Mittel
US5281631A (en) *	1991-12-20	1994-01-25	Arch Development Corp.	Phosphonic acid based ion exchange resins
US6262278B1 (en) *	1995-03-14	2001-07-17	President And Fellows Of Harvard College	Stereoselective ring opening reactions
GB9725828D0 (en)	1997-12-06	1998-02-04	Albright & Wilson Uk Ltd	Fabric treatment and polymeric compositions therefor
DE19905639A1 (de)	1999-02-11	2000-08-17	Clariant Gmbh	Wasserlösliche oder wasserquellbare Polymerisate
WO2008090152A1 (de) *	2007-01-22	2008-07-31	Basf Se	Verfahren zur herstellung von copolymeren der vinylphosphonsäure
EP2835385B1 (de)	2013-08-05	2019-12-25	Chemstream BVBA	Poly-elektrolytpolymerzusammensetzung und ihre verwendung
EP3318585A4 (de) *	2015-07-03	2018-06-20	Nissan Chemical Industries, Ltd.	Ionenkomplexmaterial mit fähigkeit zur hemmung der adhäsion von biologischen materialien und verfahren zur herstellung davon
CN108250343B (zh) *	2016-12-28	2020-06-26	江苏苏博特新材料股份有限公司	化合物、引气型共聚物及其制备方法和作为混凝土流变改性剂的应用
BR112020010126A2 (pt)	2017-12-11	2020-10-13	The Procter & Gamble Company	composições para tratamento bucal que compreendem fosfono-fosfato e polímeros contendo grupo aniônico
AU2018384632B2 (en)	2017-12-11	2021-10-21	The Procter & Gamble Company	Oral care compositions comprising phosphonate and anionic group containing polymers
US11008411B2 (en)	2017-12-11	2021-05-18	The Procter & Gamble Company	Phosphono-phosphate and anionic group containing polymers
US11046817B2 (en) *	2017-12-11	2021-06-29	The Procter & Gamble Company	Compositions comprising multi-valent cations and phosphono-phosphate containing polymers
US11046798B2 (en) *	2017-12-11	2021-06-29	The Procter & Gamble Company	Phosphono-phosphate containing compounds and polymers
US11101495B2 (en) *	2019-02-13	2021-08-24	Robert Bosch Gmbh	Phosphorous-based polyester electrolytes for high voltage lithium ion batteries

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1106963B (de) *	1959-11-11	1961-05-18	Hoechst Ag	Verfahren zur Herstellung von Polyvinylphosphonsaeure
DE1130177B (de) *	1960-03-25	1962-05-24	Hoechst Ag	Verfahren zur Herstellung von phosphorhaltigen Polymerisaten
DE1215374B (de) *	1963-07-27	1966-04-28	Hoechst Ag	Verfahren zur Herstellung phosphorhaltiger Mischpolymerisate
US3551394A (en) *	1966-07-26	1970-12-29	Nippon Zeon Co	Manufacture of high molecular weight substances
GB1569021A (en) *	1976-03-17	1980-06-11	Kuraray Co	Adhesive cementing agents containing partial phosphonic orphosphonic acid esters
DE3001894A1 (de) *	1980-01-19	1981-07-23	Hoechst Ag, 6000 Frankfurt	Verfahren zur herstellung von vinyphophonsaeurederivaten

1983
- 1983-04-22 DE DE19833314569 patent/DE3314569A1/de not_active Withdrawn
1984
- 1984-04-09 US US06/597,839 patent/US4585845A/en not_active Expired - Lifetime
- 1984-04-09 NO NO841405A patent/NO841405L/no unknown
- 1984-04-18 BR BR8401839A patent/BR8401839A/pt unknown
- 1984-04-19 DE DE8484104477T patent/DE3473154D1/de not_active Expired
- 1984-04-19 EP EP84104477A patent/EP0123297B1/de not_active Expired
- 1984-04-19 CA CA000452440A patent/CA1225794A/en not_active Expired
- 1984-04-19 AT AT84104477T patent/ATE36168T1/de not_active IP Right Cessation
- 1984-04-20 JP JP59078794A patent/JPS6042403A/ja active Pending

Also Published As

Publication number	Publication date
EP0123297A2 (de)	1984-10-31
EP0123297A3 (en)	1985-12-27
DE3473154D1 (en)	1988-09-08
EP0123297B1 (de)	1988-08-03
US4585845A (en)	1986-04-29
DE3314569A1 (de)	1984-10-25
BR8401839A (pt)	1984-11-27
NO841405L (no)	1984-10-23
JPS6042403A (ja)	1985-03-06
ATE36168T1 (de)	1988-08-15

Legal Events

Date	Code	Title	Description
2004-08-18	MKEX	Expiry

Publication	Publication Date	Title
CA1225794A (en)	1987-08-18	Crosslinked hydrophilic copolymers, their preparation and their use
US4518745A (en)	1985-05-21	Metal chelates of water soluble copolymers
US4722958A (en)	1988-02-02	Process for the preparation of copolymers
CA1267483A (en)	1990-04-03	Process for the production of a water-soluble polymer dispersion
Khokhlov et al.	1992	Collapse of polyelectrolyte networks induced by their interaction with oppositely charged surfactants
ES2223627T3 (es)	2005-03-01	Metodo para producir polimeros hidrofobamente asociativos, metodos de uso y composiciones.
US5763523A (en)	1998-06-09	Stable emulsion blends and methods for their use
US4956399A (en)	1990-09-11	Emulsified mannich acrylamide polymers
US4357245A (en)	1982-11-02	Water-soluble copolymer and its preparation
EP0763548B1 (de)	2000-03-08	Mikroemulgierte funktionalisierte Polymere
WO2013138156A1 (en)	2013-09-19	Synthesis and application of high pressure high temperature fluid loss additive and rheology stabilizer
USRE36884E (en)	2000-09-26	Mannich acrylamide polymers
US4743666A (en)	1988-05-10	Water-soluble copolymers with pendant phosphonic, sulphonic and amide groups
US5132023A (en)	1992-07-21	Emulsified mannich acrylamide polymers
JPH0651755B2 (ja)	1994-07-06	水溶性カチオンポリマー分散液の製造方法
GB2081725A (en)	1982-02-24	A Process for the Production of a Hydrogel
DE4034642A1 (de)	1992-05-07	Wasserloesliche mischpolymerisate und deren verwendung
CN106866881A (zh)	2017-06-20	疏水缔合丙烯酰胺类聚合物乳液及其制备方法
US3691124A (en)	1972-09-12	Stabilized polymer in oil latexes and suspensions
US4879361A (en)	1989-11-07	Preparation of bead polymers from water-soluble, ethylenically unsaturated monomers
EP1492828B1 (de)	2005-11-16	Wasserlösliche copolymere auf basis von olefinischen sulfonsäuren, verfahren zu deren herstellung und ihre verwendung
JPS63251409A (ja)	1988-10-18	カチオン性オリゴマ−
US4522997A (en)	1985-06-11	Crosslinking agents for water-swellable polymers
RU2060258C1 (ru)	1996-05-20	Способ получения полимера с функциональными группами, способными сшивать указанный полимер
NO842737L (no)	1985-01-23	Fosfonsyregrupper inneholdende polymerisater, deres fremgangsmaate og fremstilling